Islesboro Vacation Packages

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Your Islesboro Vacation

When you organize a vacation package to Islesboro, you can relax and enjoy your getaway knowing your travel plans are in order. Discover the many charms of this amazing city from your base in a neighborhood like Bayside, which is great for history. If sightseeing is on the agenda during your trip to Islesboro, stop by major attractions like Windsor Chairmakers, Schoolhouse Museum and Warren Island State Park. A few quick clicks is all it takes to build your ideal Islesboro vacation on Expedia.

Top Islesboro Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Country Inn at The Mall

Country Inn at The Mall

2 out of 5
per person
Oct 5 - Oct 11
just found
Roundtrip non-stop flight included
Montreal (YMQ) to Bangor (BGR)
9.4/10 Exceptional! (2,315 reviews)
I always stay at this hotel when I visit Bangor. Not only are the rooms exceptional, the breakfast is very good too.

Reviewed on Jul. 20, 2025

Hilton Garden Inn Bangor

Hilton Garden Inn Bangor

3 out of 5
per person
Oct 5 - Oct 11
just found
Roundtrip non-stop flight included
Montreal (YMQ) to Bangor (BGR)
9/10 Wonderful! (1,000 reviews)
Would stay here again

Reviewed on Jul. 20, 2025

Hollywood Casino Bangor

Hollywood Casino Bangor

3 out of 5
per person
Sep 7 - Sep 14
found 21 hours ago
Roundtrip flight included
Toronto (YYZ) to Bangor (BGR)
8.6/10 Excellent! (1,150 reviews)
The staff was so very helpful!! It's easily walkable to downtown and lots of dining options.

Reviewed on Jul. 20, 2025

Camp DeForest

Camp DeForest

3.5 out of 5
per person
Oct 5 - Oct 11
just found
Roundtrip non-stop flight included
Montreal (YMQ) to Bangor (BGR)
No reviews
Sugarloaf Mountain Hotel

Sugarloaf Mountain Hotel

3.5 out of 5
per person
Sep 7 - Sep 14
found 21 hours ago
Roundtrip flight included
Toronto (YYZ) to Bangor (BGR)
9.2/10 Wonderful! (509 reviews)
Check in is not the best. There never anybody at the reception. You have to wait and they come from i don't know where. Weird

Reviewed on Jul. 13, 2025

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Islesboro Hotel Deals

Island log home in Maine with ocean views

Island log home in Maine with ocean views

Islesboro
9.8/10 Exceptional! (73 reviews)
Maine Vacation
"Loved the island life! Would return it was great!"

Reviewed on Jul. 14, 2025

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Island log home in Maine with ocean views
Belfast Harbor Inn

Belfast Harbor Inn

3.5 out of 5
91 Searsport Ave, Belfast, ME
Fully refundableReserve now, pay when you stay
The price is CA $246 per night from Jul 27 to Jul 28
CA $246
CA $268 total
Jul 27 - Jul 28
includes taxes & fees
9.6/10 Exceptional! (1,001 reviews)
"This hotel is located on water, located near Belfast which has great restaurants, friendly people and a nice city park on the bay."

Reviewed on Jul. 18, 2025

Belfast Harbor Inn
The Country Inn at Camden Rockport

The Country Inn at Camden Rockport

2.5 out of 5
8 Country Inn Way, Rockport, ME
The price is CA $301 per night from Jul 28 to Jul 29
CA $301
CA $328 total
Jul 28 - Jul 29
includes taxes & fees
9.4/10 Exceptional! (1,006 reviews)
"Na"

Reviewed on Jul. 18, 2025

The Country Inn at Camden Rockport
See all 1,355 properties in Islesboro
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does an Islesboro vacation package cost?
Offering great value package deals from CA $868 on Expedia, you'll be thrilled with how little a vacation to Islesboro costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Islesboro?
Plan your trip for the low or shoulder season and you're likely to find cheap Islesboro vacation packages. Keep in mind that school vacation periods and local events and festivals can have an impact on prices, so do your research before you go.
How many days is enough for Islesboro?
The ideal duration of your Islesboro vacation depends on what you'd like to do and see. Typically, a handful of days to a week will give you enough time to visit all the main attractions and discover some hidden gems along the way.
How to find the best Islesboro package deals?
Use Expedia's filters to help you find some of the best Islesboro package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or browse for Islesboro package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book an Islesboro vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and hotels separately. Better still, you can customize your Islesboro getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Islesboro?
If you have your Islesboro vacation dates locked in, book early to bag some unbeatable deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Islesboro?

  1. Choose the best time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Islesboro.
  2. Work out your budget: Make sure you have enough money to pay for everything from transportation and dining out to airfares and activities. Your hotel will likely be the biggest expense during your trip to Islesboro.
  3. Decide your trip length: Consider how much time you'd like to spend discovering Islesboro. Plan your itinerary so you can get to all the attractions and experiences you're interested in without rushing.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to pick an Islesboro vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.